JPS6129327B2 - - Google Patents
Info
- Publication number
- JPS6129327B2 JPS6129327B2 JP53096592A JP9659278A JPS6129327B2 JP S6129327 B2 JPS6129327 B2 JP S6129327B2 JP 53096592 A JP53096592 A JP 53096592A JP 9659278 A JP9659278 A JP 9659278A JP S6129327 B2 JPS6129327 B2 JP S6129327B2
- Authority
- JP
- Japan
- Prior art keywords
- heparin
- salt
- calcium
- solution
- oxalate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 187
- 229920000669 heparin Polymers 0.000 claims description 174
- 229960002897 heparin Drugs 0.000 claims description 125
- 239000000243 solution Substances 0.000 claims description 108
- 150000003839 salts Chemical class 0.000 claims description 66
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 39
- 229910052751 metal Inorganic materials 0.000 claims description 38
- 239000002184 metal Substances 0.000 claims description 38
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 33
- 239000011707 mineral Substances 0.000 claims description 33
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 31
- 239000011575 calcium Substances 0.000 claims description 31
- 229910052791 calcium Inorganic materials 0.000 claims description 31
- 239000002244 precipitate Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000003860 storage Methods 0.000 claims description 13
- 239000013078 crystal Substances 0.000 claims description 10
- 150000002739 metals Chemical class 0.000 claims description 10
- 159000000007 calcium salts Chemical class 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 150000003891 oxalate salts Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
- 238000000034 method Methods 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 31
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- 238000003756 stirring Methods 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- -1 oxalate ions Chemical class 0.000 description 15
- 230000007935 neutral effect Effects 0.000 description 13
- 238000001556 precipitation Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000005194 fractionation Methods 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- 239000006228 supernatant Substances 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 9
- 238000011282 treatment Methods 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 7
- 229940100630 metacresol Drugs 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical compound [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical compound [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- 239000012906 subvisible particle Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011833 salt mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OHJKXVLJWUPWQG-PNRHKHKDSA-N Heparinsodiumsalt Chemical compound O[C@@H]1[C@@H](NS(O)(=O)=O)[C@@H](O)O[C@H](COS(O)(=O)=O)[C@H]1O[C@H]1[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O)[C@H](C(O)=O)O1 OHJKXVLJWUPWQG-PNRHKHKDSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000012905 visible particle Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33170/77A GB1602439A (en) | 1977-08-08 | 1977-08-08 | Purified heparin |
| GB5204777 | 1977-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5446809A JPS5446809A (en) | 1979-04-13 |
| JPS6129327B2 true JPS6129327B2 (xx) | 1986-07-05 |
Family
ID=26261753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9659278A Granted JPS5446809A (en) | 1977-08-08 | 1978-08-08 | Purifying of heparine |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4652555A (xx) |
| JP (1) | JPS5446809A (xx) |
| AT (1) | AT371713B (xx) |
| AU (1) | AU529432B2 (xx) |
| CA (1) | CA1105453A (xx) |
| CH (1) | CH636888A5 (xx) |
| DE (1) | DE2834702A1 (xx) |
| DK (1) | DK350078A (xx) |
| ES (1) | ES472430A1 (xx) |
| FR (1) | FR2400036A1 (xx) |
| IE (1) | IE47169B1 (xx) |
| IT (1) | IT1192564B (xx) |
| NL (1) | NL7808292A (xx) |
| SE (1) | SE447872B (xx) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2461719A2 (fr) * | 1979-07-20 | 1981-02-06 | Choay Sa | Composition mucopolysaccharidique ayant une activite regulatrice de la coagulation, medicament la contenant et procede pour l'obtenir |
| EP0245813B2 (en) * | 1986-05-16 | 2000-03-22 | ITALFARMACO S.p.A. | EDTA-free heparins, heparin fractions and fragments, processes for their preparation and pharmaceutical compositions containing them |
| AR243204A1 (es) * | 1986-11-21 | 1993-07-30 | Ajorca Sa | Un metodo para la depolimerizacion quimica de polisacaridos. |
| SE8702254D0 (sv) * | 1987-05-29 | 1987-05-29 | Kabivitrum Ab | Novel heparin derivatives |
| USRE38743E1 (en) | 1990-06-26 | 2005-06-14 | Aventis Pharma S.A. | Mixtures of particular LMW heparinic polysaccharides for the prophylaxis/treatment of acute thrombotic events |
| JP2001231595A (ja) * | 1999-12-15 | 2001-08-28 | Fuaruko Bio Syst:Kk | 特異的破骨細胞由来酸性ホスファターゼの測定方法 |
| EP2284535A1 (en) * | 2002-03-11 | 2011-02-16 | Momenta Pharmaceuticals, Inc. | Low molecular weight heparins |
| US9139876B1 (en) | 2007-05-03 | 2015-09-22 | Momenta Pharmacueticals, Inc. | Method of analyzing a preparation of a low molecular weight heparin |
| WO2009141821A1 (en) * | 2008-05-20 | 2009-11-26 | Crystal Clear Partnership | Separation of polysaccharides by charge density gradient |
| ES2340902B1 (es) | 2008-07-01 | 2011-05-03 | Laboratorios Farmaceuticos Rovi, S.A. | Composicion farmaceutica con glicosaminoglicanos y su uso en tratamiento de ulceras cronicas. |
| CN102791742B (zh) * | 2010-01-19 | 2014-12-24 | 动量制药公司 | 评价肝素制剂 |
| KR101794877B1 (ko) * | 2010-09-14 | 2017-11-07 | 고쿠리츠 다이가쿠 호징 미야자키 다이가쿠 | 고순도 헤파린 및 그 제조방법 |
| WO2012115952A1 (en) | 2011-02-21 | 2012-08-30 | Momenta Pharmaceuticals, Inc. | Evaluating heparin preparations |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135660A (en) * | 1956-11-09 | 1964-06-02 | Riker Laboratories Inc | Method for purifying sulfated carbohydrates with oxidizing agents |
| US3482014A (en) * | 1966-06-29 | 1969-12-02 | Canada Packers Ltd | Orally active heparin and method for making and using same |
| CA1042001A (en) * | 1973-04-13 | 1978-11-07 | Choay S.A. | Mixed heparin salts |
| FR2225406A1 (en) * | 1973-04-13 | 1974-11-08 | Choay Sa | Sodium-free heparin salts - by cation exchange of sodium salts, anticoagulants without side-effects |
-
1978
- 1978-08-08 DE DE19782834702 patent/DE2834702A1/de active Granted
- 1978-08-08 SE SE7808487A patent/SE447872B/sv not_active IP Right Cessation
- 1978-08-08 FR FR7823396A patent/FR2400036A1/fr active Granted
- 1978-08-08 IT IT26580/78A patent/IT1192564B/it active
- 1978-08-08 CA CA308,923A patent/CA1105453A/en not_active Expired
- 1978-08-08 JP JP9659278A patent/JPS5446809A/ja active Granted
- 1978-08-08 AT AT0577078A patent/AT371713B/de not_active IP Right Cessation
- 1978-08-08 IE IE1616/78A patent/IE47169B1/en not_active IP Right Cessation
- 1978-08-08 ES ES472430A patent/ES472430A1/es not_active Expired
- 1978-08-08 NL NL787808292A patent/NL7808292A/xx not_active Application Discontinuation
- 1978-08-08 CH CH841878A patent/CH636888A5/fr not_active IP Right Cessation
- 1978-08-08 DK DK350078A patent/DK350078A/da not_active Application Discontinuation
- 1978-08-08 AU AU38748/78A patent/AU529432B2/en not_active Expired
-
1982
- 1982-12-22 US US06/452,197 patent/US4652555A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2400036A1 (fr) | 1979-03-09 |
| SE447872B (sv) | 1986-12-22 |
| DK350078A (da) | 1979-02-09 |
| FR2400036B1 (xx) | 1980-09-19 |
| IE781616L (en) | 1979-02-08 |
| IT1192564B (it) | 1988-04-20 |
| IE47169B1 (en) | 1984-01-11 |
| JPS5446809A (en) | 1979-04-13 |
| NL7808292A (nl) | 1979-02-12 |
| DE2834702A1 (de) | 1979-02-22 |
| AU529432B2 (en) | 1983-06-09 |
| ATA577078A (de) | 1982-12-15 |
| CH636888A5 (fr) | 1983-06-30 |
| AU3874878A (en) | 1980-02-14 |
| ES472430A1 (es) | 1979-03-16 |
| AT371713B (de) | 1983-07-25 |
| DE2834702C2 (xx) | 1988-11-10 |
| SE7808487L (sv) | 1979-02-09 |
| CA1105453A (en) | 1981-07-21 |
| IT7826580A0 (it) | 1978-08-08 |
| US4652555A (en) | 1987-03-24 |
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